JPH0597827A - 新規の薬学活性成分としての２−イミノチアゾリジン−４−オン誘導体 - Google Patents
新規の薬学活性成分としての２−イミノチアゾリジン−４−オン誘導体Info
- Publication number
- JPH0597827A JPH0597827A JP4087445A JP8744592A JPH0597827A JP H0597827 A JPH0597827 A JP H0597827A JP 4087445 A JP4087445 A JP 4087445A JP 8744592 A JP8744592 A JP 8744592A JP H0597827 A JPH0597827 A JP H0597827A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- alk
- hydrogen
- alkyl
- pharmaceutically acceptable
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000004480 active ingredient Substances 0.000 title description 32
- HYMJHROUVPWYNQ-UHFFFAOYSA-N 2-amino-1,3-thiazol-4-one Chemical class NC1=NC(=O)CS1 HYMJHROUVPWYNQ-UHFFFAOYSA-N 0.000 title description 2
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 69
- 150000003839 salts Chemical class 0.000 claims abstract description 67
- 150000001875 compounds Chemical class 0.000 claims abstract description 44
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 42
- 239000001257 hydrogen Substances 0.000 claims abstract description 42
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 29
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 24
- 201000010099 disease Diseases 0.000 claims abstract description 19
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 19
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 12
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims description 52
- -1 2-bromo isobutyl Chemical group 0.000 claims description 32
- 125000005237 alkyleneamino group Chemical group 0.000 claims description 32
- 238000004519 manufacturing process Methods 0.000 claims description 27
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 26
- 239000008194 pharmaceutical composition Substances 0.000 claims description 20
- WKCGPFOFWXAUDX-UHFFFAOYSA-N 1,1'-dithiobis Chemical compound S1C(S2)(C)CC(C)(S3)SC2(C)SC13SSC(S1)(S2)SC3(C)SC1(C)CC2(C)S3 WKCGPFOFWXAUDX-UHFFFAOYSA-N 0.000 claims description 15
- 241000534944 Thia Species 0.000 claims description 13
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 12
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 9
- 239000003826 tablet Substances 0.000 claims description 8
- 239000002775 capsule Substances 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 125000004970 halomethyl group Chemical group 0.000 claims description 6
- 125000005394 methallyl group Chemical group 0.000 claims description 6
- 239000002552 dosage form Substances 0.000 claims description 5
- 239000008298 dragée Substances 0.000 claims description 5
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 125000001475 halogen functional group Chemical group 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 238000007911 parenteral administration Methods 0.000 claims description 4
- 239000007924 injection Substances 0.000 claims description 3
- 238000002347 injection Methods 0.000 claims description 3
- 239000000829 suppository Substances 0.000 claims description 3
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims description 2
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 2
- 239000007940 sugar coated tablet Substances 0.000 claims description 2
- 230000000996 additive effect Effects 0.000 claims 1
- 239000003978 infusion fluid Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 description 41
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 19
- 239000000203 mixture Substances 0.000 description 17
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 16
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 10
- 239000008101 lactose Substances 0.000 description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 9
- 235000019359 magnesium stearate Nutrition 0.000 description 8
- 239000000454 talc Substances 0.000 description 7
- 229910052623 talc Inorganic materials 0.000 description 7
- 235000012222 talc Nutrition 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 229920000159 gelatin Polymers 0.000 description 6
- 235000019322 gelatine Nutrition 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 108010010803 Gelatin Proteins 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
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- 235000011852 gelatine desserts Nutrition 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
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- 239000002202 Polyethylene glycol Substances 0.000 description 4
- 208000025747 Rheumatic disease Diseases 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 4
- 239000004141 Sodium laurylsulphate Substances 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 230000002456 anti-arthritic effect Effects 0.000 description 4
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- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 4
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 4
- 235000019698 starch Nutrition 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 230000000259 anti-tumor effect Effects 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 3
- 239000008116 calcium stearate Substances 0.000 description 3
- 235000013539 calcium stearate Nutrition 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000007941 film coated tablet Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 230000001506 immunosuppresive effect Effects 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 3
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 3
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- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000000600 sorbitol Substances 0.000 description 3
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- 239000003381 stabilizer Substances 0.000 description 3
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- 206010065553 Bone marrow failure Diseases 0.000 description 2
- 102000000589 Interleukin-1 Human genes 0.000 description 2
- 108010002352 Interleukin-1 Proteins 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
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- 235000021355 Stearic acid Nutrition 0.000 description 2
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- 150000007513 acids Chemical class 0.000 description 2
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- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
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- 229940057995 liquid paraffin Drugs 0.000 description 2
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- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
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- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 2
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- 239000013583 drug formulation Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
- 229940093471 ethyl oleate Drugs 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005446 heptyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 229940031704 hydroxypropyl methylcellulose phthalate Drugs 0.000 description 1
- 229920003132 hydroxypropyl methylcellulose phthalate Polymers 0.000 description 1
- 230000004957 immunoregulator effect Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 description 1
- 201000004990 juvenile ankylosing spondylitis Diseases 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 201000002364 leukopenia Diseases 0.000 description 1
- 231100001022 leukopenia Toxicity 0.000 description 1
- 206010025135 lupus erythematosus Diseases 0.000 description 1
- 210000005210 lymphoid organ Anatomy 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 150000002690 malonic acid derivatives Chemical class 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 229960002900 methylcellulose Drugs 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 210000001616 monocyte Anatomy 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 230000001613 neoplastic effect Effects 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229940116317 potato starch Drugs 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 208000002574 reactive arthritis Diseases 0.000 description 1
- 230000000552 rheumatic effect Effects 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229940100486 rice starch Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 201000005671 spondyloarthropathy Diseases 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000005505 thiomorpholino group Chemical group 0.000 description 1
- 210000001685 thyroid gland Anatomy 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH108791 | 1991-04-12 | ||
| CH01087/91-2 | 1991-04-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0597827A true JPH0597827A (ja) | 1993-04-20 |
Family
ID=4202162
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4087445A Pending JPH0597827A (ja) | 1991-04-12 | 1992-04-09 | 新規の薬学活性成分としての２−イミノチアゾリジン−４−オン誘導体 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US5229405A (en, 2012) |
| EP (1) | EP0508955B1 (en, 2012) |
| JP (1) | JPH0597827A (en, 2012) |
| KR (1) | KR920019353A (en, 2012) |
| AT (1) | ATE139441T1 (en, 2012) |
| AU (1) | AU658175B2 (en, 2012) |
| CA (1) | CA2065798A1 (en, 2012) |
| DE (1) | DE59206593D1 (en, 2012) |
| DK (1) | DK0508955T3 (en, 2012) |
| ES (1) | ES2088567T3 (en, 2012) |
| GR (1) | GR3020292T3 (en, 2012) |
| IE (1) | IE75692B1 (en, 2012) |
| IL (1) | IL101506A (en, 2012) |
| TW (1) | TW225989B (en, 2012) |
| ZA (1) | ZA922625B (en, 2012) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU665073B2 (en) * | 1992-06-03 | 1995-12-14 | Ciba-Geigy Ag | Novel thiosemicarbazone derivatives |
| AU664084B2 (en) * | 1992-06-03 | 1995-11-02 | Ciba-Geigy Ag | Novel thiosemicarbazonic acid esters |
| NZ256400A (en) * | 1992-10-06 | 1996-11-26 | Ciba Geigy Ag | 4-thiothiazolidin-2-ylidene thiosemicarbazone derivatives and medicaments |
| HUT71608A (en) * | 1993-11-25 | 1996-01-29 | Ciba Geigy Ag | Novel substituted thiosemicarbazone derivatives, process for producing them and pharmaceutical compositions containing them |
| HUT71600A (en) * | 1993-11-25 | 1996-01-29 | Ciba Geigy Ag | Novel substituted thiosemicarbanozic acid esters, process for producing them and pharmaceutical compositions containing them |
| JPH08506359A (ja) * | 1993-11-25 | 1996-07-09 | チバ−ガイギー アクチェンゲゼルシャフト | 新規置換化チオセミカルバゾンチオン類 |
| EP0753147A1 (en) * | 1994-03-30 | 1997-01-15 | Novartis AG | Screening method using the rzr receptor family |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3699116A (en) * | 1965-10-29 | 1972-10-17 | Ciba Geigy Corp | 2,2'-azines of 2,4-thiazolidinediones |
| CH511877A (de) * | 1969-07-17 | 1971-08-31 | Ciba Geigy Ag | Verfahren zur Herstellung eines neuen Thiosemicarbazons |
| GB1257971A (en, 2012) * | 1969-07-18 | 1971-12-22 | ||
| CH579063A5 (en, 2012) * | 1973-02-13 | 1976-08-31 | Ciba Geigy Ag | |
| AR204619A1 (es) * | 1973-02-13 | 1976-02-20 | Ciba Geigy Ag | Procedimiento para la elaboracion de un nuevo derivado de 2,2-azina-2,4-tiazolidindiona |
| DE2632745A1 (de) * | 1975-08-06 | 1977-02-24 | Ciba Geigy Ag | 1,1'-dithiobis-(formamid-hydrazone) |
| DE2632747A1 (de) * | 1975-08-06 | 1977-02-24 | Ciba Geigy Ag | Azine von sechs- und siebengliedrigen thiazaheterocyclen |
| DE2632746A1 (de) * | 1975-08-06 | 1977-02-24 | Ciba Geigy Ag | Methylen- oder substituierte methyl-thiazaheterocyclyl-azine |
| DE3064485D1 (en) * | 1979-07-04 | 1983-09-08 | Erba Farmitalia | Anthracycline glycosides, process for their preparation and therapeutical composition containing them |
| EP0085275B1 (de) * | 1982-01-22 | 1986-02-19 | Ciba-Geigy Ag | Substituierte Thiazolidinylester von Mineralsäuren |
| US4582841A (en) * | 1983-07-19 | 1986-04-15 | Ciba-Geigy Corporation | Substituted thiazolidinyl esters of mineral acids |
-
1992
- 1992-03-30 AU AU13906/92A patent/AU658175B2/en not_active Ceased
- 1992-04-03 ES ES92810257T patent/ES2088567T3/es not_active Expired - Lifetime
- 1992-04-03 AT AT92810257T patent/ATE139441T1/de not_active IP Right Cessation
- 1992-04-03 DE DE59206593T patent/DE59206593D1/de not_active Expired - Fee Related
- 1992-04-03 DK DK92810257.3T patent/DK0508955T3/da not_active Application Discontinuation
- 1992-04-03 EP EP92810257A patent/EP0508955B1/de not_active Expired - Lifetime
- 1992-04-06 IL IL10150692A patent/IL101506A/en not_active IP Right Cessation
- 1992-04-09 JP JP4087445A patent/JPH0597827A/ja active Pending
- 1992-04-09 TW TW081102728A patent/TW225989B/zh active
- 1992-04-10 CA CA002065798A patent/CA2065798A1/en not_active Abandoned
- 1992-04-10 ZA ZA922625A patent/ZA922625B/xx unknown
- 1992-04-10 IE IE921165A patent/IE75692B1/en not_active IP Right Cessation
- 1992-04-10 US US07/866,926 patent/US5229405A/en not_active Expired - Fee Related
- 1992-04-11 KR KR1019920006034A patent/KR920019353A/ko not_active Ceased
-
1996
- 1996-06-20 GR GR960401463T patent/GR3020292T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK0508955T3 (da) | 1996-07-15 |
| GR3020292T3 (en) | 1996-09-30 |
| DE59206593D1 (de) | 1996-07-25 |
| IE921165A1 (en) | 1992-10-21 |
| TW225989B (en, 2012) | 1994-07-01 |
| ES2088567T3 (es) | 1996-08-16 |
| IL101506A (en) | 1996-08-04 |
| IL101506A0 (en) | 1992-12-30 |
| EP0508955B1 (de) | 1996-06-19 |
| ATE139441T1 (de) | 1996-07-15 |
| AU1390692A (en) | 1992-10-15 |
| EP0508955A1 (de) | 1992-10-14 |
| ZA922625B (en) | 1992-11-25 |
| AU658175B2 (en) | 1995-04-06 |
| KR920019353A (ko) | 1992-11-19 |
| US5229405A (en) | 1993-07-20 |
| CA2065798A1 (en) | 1992-10-13 |
| IE75692B1 (en) | 1997-09-10 |
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